Ethyl 2-aminothiazole-4-carboxylate → Ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate

HRID 1667004Notes

Reaction equation

HRID 1667004 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23])=O>C(C(C)=O)C>[CH2:10]([O:9][C:7]([C:5]1[N:6]2[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-:24])=[O:23])[N:1]=[C:2]2[S:3][CH:4]=1)=[O:8])[CH3:11]

Participants

4

Reactant 2

HCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 2440252-Bromo-2'-nitroacetophenone

Product 1

HCID 25232522Ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylateYield 79.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a typical run, 2.1 g of ethyl 2-aminothiazole-4-carboxylate (Combi-Blocks, 0.0123 mol) was mixed with 25 mL of methyl ethyl ketone along with 2-bromo-2′-nitroacetophenone (3.0 g, 0.0123 mol). The reaction mixture was stirred under reflux for 18 hours. It was then cooled to room temperature and filtered to remove some of the solids. The filtrate was concentrated to afford 3.10 g of 6-(2-nitro-phenyl)-imidazo[2,1-b]thiazole-3-carboxylic acid ethyl ester (MS, M++H=318).

Workup

  1. temperatureunder reflux for 18 hours
  2. filtrationfiltered
  3. customto remove some of the solids
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d2a973c6d6ac4b0ab7e483a73c6cdf4c
Source dataset
uspto-grants-2011_10
Patent number
US08044198B2

Reaction notes

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